The Facebook IPO debacle continues to cost money and scalps. And, once again, as with every Wall Street scandal, dumb emails are involved. Thank you, Wall Street, for never learning your lesson on that one.

The other, more serious lesson from this particular episode is that the way Wall Street communicates with investors and the public is still a giant mess, nearly a decade after regulatory reforms meant to clean that mess up.

Citigroup on Friday agreed to pay $2 million to settle charges by the Massachusetts Secretary of the Commonwealth William F. Galvin that it had failed to properly supervise its analysts, one of whom allegedly disclosed confidential information about Facebook ahead of its disastrous May IPO.

Citi has also fired Mark Mahaney, a senior analyst covering Internet companies including Facebook and Google, the Wall Street Journal reported. Mahaney was not cited by name in Galvin's complaint, but a "senior analyst" matching Mahaney's description was discussed early and often -- including several dumb emails.

Last month, Citi also fired an unnamed junior analyst who, according to Galvin's complaint, disclosed confidential information about Facebook to a couple of TechCrunch bloggers before the IPO. And, you guessed it, that junior analyst sent some dumb emails! (AOL is the parent company of both TechCrunch and The Huffington Post.)

Specifically, on May 2, a couple of weeks before Facebook's IPO, Unnamed Junior Analyst ("UJA" hereafter, but probably someone named Eric Jacobs, according to Business Insider) emailed TechCrunch bloggers a one-page summary of Citigroup's thesis about Facebook. He said he wanted to get their opinion about whether they had the risks and rewards of Facebook right.

"I am ramping up coverage on FB and thought you guys might like to see how the street is thinking about it (and our estimates)," UJA wrote. "Any feedback on the investment positives and risks would be super helpful. I want to make sure I'm thinking about this the right way. This, of course is confidential."

I just want to stop right here and allow you to consider that this is a person paid, probably extremely well, by Citigroup to analyze companies, and he is asking a couple of bloggers -- very, very smart bloggers! -- for their help.

Anyway, based on the description of the bloggers in Galvin's complaint, one of those TechCrunch bloggers would appear to be Josh Constine, a Stanford graduate like UJA, and a former writer for Inside Facebook. Constine did not immediately respond to a request for comment.

According to the complaint, that TechCrunch blogger asked to publish Citi's thesis, sourcing it anonymously.

"My boss would eat me alive," UJA wrote.

The TechCrunch blogger asked UJA, just for clarity, if this was really Citi's thesis on Facebook, and UJA responded that it was an outline that "will eventually become our initiation report at 30-40 pages."

Ultimately, Mahaney's first report on Facebook, released on June 27, gave the stock a "neutral" rating, calling the company's challenges "significant" and saying the stock was only worth $35, or $3 less than its IPO price.

Citigroup handed all of these emails to Galvin in response to a subpoena looking for information about the Facebook IPO, which is the subject of several regulatory probes and lawsuits. Facebook's stock suffered through volatile trading on its first day and then lost 53 percent of its value in the next three months. Facebook, its underwriters and Nasdaq-OMX face dozens of lawsuits over the IPO. Meanwhile, regulators are investigating whether the banks leading the IPO warned a select group of investors about Facebook's risks, while pumping the stock to the general public, creating a media frenzy.

Ironically, Citi got fined $2 million for its analysts possibly tipping the public off to those risks, via TechCrunch. TechCrunch did not ultimately reveal Citi's cautious take on the stock, but imagine if it had -- maybe some of the air would have come out of the Facebook bubble before its IPO.

But there are still apparently giant holes that allow some pertinent information to get to select investors, while the unaware public is still at risk of getting caught up in an IPO frenzy.

Ultimately, Unnamed Junior Analyst got fired, as did his boss, Unnamed Senior Analyst. According to the complaint, he had some compliance issues of his own. In one instance, according to the complaint, he appeared to mislead a Citi public-relations employee about whether he had already responded to some questions from a French reporter about YouTube, a unit of Google. According to the complaint, he also tried unsuccessfully to get that PR employee to pretend he hadn't yet responded to the questions, emailing: "Shoot. This could get me into trouble. Shoot."

That, and the Facebook IPO, did apparently get him into some trouble.

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10 Bankers Behind Bars

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In what is now considered to be one of the biggest and most famous Ponzi schemes in history, Madoff laundered about $65 billion, Forbes reports. Madoff defrauded thousands of investors, all of whom can be found on a 163-page list.

Ex-Goldman Rajat Gupta was sentenced to two years in prison for participating in one of the largest insider trading schemes in history.

Kerviel was found guilty of one of the world's most colosal trading frauds in 2010. He cost France's Société Générale bank 4.9 billion Euros. He was sentenced to 3 years in jail and was also sentenced to paying a $7 billion fine, The Guardian reports.

Goldberg, Grimm and Carollo were found guilty of conning the I.R.S. and cities in a "bid-rigging scheme" during their time at General Electric, Businessweek reports.
Goldberg was sentenced to four years in prison. Grimm and Carollo were each sentenced to three years.

Raj Rajaratnam, the former head of Galleon Management, was sentenced to 11 years in jail in October 2011, the longest prison term for insider trading to date, The Washington Post reports.

During Nick Lesson's time at Bristain's Barings Bank, he lost 862 million pounds and even managed to level the 233-year-old bank itself, according to The Telegraph. He served four years in a Singapore jail before he was released early with life-threatening cancer.

Currently serving 110 years in prison, Allen Stanford was, at one time, one of the richest men in America, according to CNBC. He conned about 20,000 investors out of their money in a Ponzi scheme.

Garth Peterson, the former head of Morgan Stanley's Chinese real-estate investments unit, was sentenced to 9 months in jail last August for bribery, according to The Wall Street Journal.

Bradley Birkenfeld spent more than 2 years in jail for assisting in income tax evasion while working at UBS. He then volunteered inside information on Swiss banking to the I.R.S., and was rewarded with $104 million for being a whistle-blower, according to The New York Times.

Dennis Levine, Martin Siegel, Ivan Boesky and Michael Milken defrauded Wall Street investors in the 1980's. In a scandalous series of events, Levine stole confidential documents from Lazard Freres investment bank, and the crew made use of inside information, according to The Daily Beast.